Ashland holiday rentals

We found 50 holiday rentals — enter your dates for availability
Discover a selection of 12 homes and other holiday rentals in Ashland that are perfect for your trip. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as Wi-Fi and parking. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.

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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

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Cosy Ashland will entice you

Enjoy the architecture and other features of Ashland. This city is well-known for its lake and hiking. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Ashland

Are you looking for attractions to visit while you're in town? Venture out of your cosy holiday rental and check out everything that makes Ashland a one-of-a-kind holiday spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Mount Ashwabay Ski and Recreation Area (12.7 mi / 20.5 km)
  • Whitecap Mountains (26.2 mi / 42.2 km)
  • Ashland Mural Walk (0.3 mi / 0.4 km)
  • Chequamegon Bay Golf Course (2.1 mi / 3.4 km)
  • Apostle Highlands Golf Course (15.2 mi / 24.5 km)

Exploring the natural features in Ashland

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Ashland is a great place to get outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Houghton Falls Nature Preserve (4.7 mi / 7.6 km)
  • Chequamegon Bay (5.6 mi / 9 km)
  • Copper Falls State Park (20 mi / 32.3 km)
  • Whitecap Mountains (26.2 mi / 42.2 km)
  • Lake Namakagon (28.2 mi / 45.4 km)
  • Chequamegon National Forest (29.8 mi / 48 km)

Travelling to and around Ashland

The nearest airport is in Ironwood, MI (IWD-Gogebic County), located 35.9 mi (57.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Ashland when booking a holiday rental?
When considering a holiday rental in Ashland, Wisconsin, the downtown area is an excellent choice. This vibrant neighbourhood offers a charming mix of local shops, cafes, and restaurants, making it an ideal spot for visitors who want to immerse themselves in the local culture. Staying here provides easy access to the stunning views of Lake Superior, which is a major attraction in the area.Another appealing neighbourhood is the Ashland Historic District, known for its beautiful architecture and rich history. Here, you can explore historic buildings and enjoy the scenic beauty of the nearby Chequamegon National Forest. This area is also close to the Ashland Marina, where you can partake in various water activities or simply relax by the lake.In terms of holiday rentals, there are numerous options available in both of these neighbourhoods, suiting a range of preferences and budgets.
Where are the best areas for renting a beach house in Ashland?
For renting a beach house in Ashland, Wisconsin, the area along the shores of Lake Superior offers some delightful options. Particularly, the Apostle Islands National Lakeshore provides a stunning backdrop with its picturesque landscapes and opportunities for outdoor activities. In Ashland, you can find properties that come with amenities such as spacious decks for enjoying the lake views, fire pits for evening gatherings, and fully equipped kitchens for those who wish to self-cater.In the nearby Chequamegon Bay, there are charming cottages and modern homes available for rent, many of which are just a short walk from the water's edge. These properties often feature amenities like private docks for boating, outdoor grills for summer barbecues, and family-friendly spaces to accommodate larger groups. The bay area is also home to local shops and restaurants, providing convenience for those staying in the area.Additionally, Ashland's proximity to the scenic Bayfield Peninsula allows for easy day trips to explore the beautiful beaches and hiking trails of the Apostle Islands. Rentals in this region frequently offer a blend of rustic charm and modern comfort, making them ideal for travellers looking to immerse themselves in the natural beauty of Wisconsin's north shore while enjoying the recreational activities that Lake Superior has to offer.
Where are the best Ashland ski resort rentals?
For the best ski resort rentals near Ashland, Wisconsin, consider looking in the nearby area of Telemark Resort, located just a short drive away. This resort offers various types of accommodations, including lodge rooms and spacious condos, superb for families or groups. Many of these rentals come equipped with modern amenities such as full kitchens, fireplaces, and easy access to ski trails, allowing guests to enjoy a comfortable and convenient stay.In Ashland itself, you can find charming cabins and homes that provide a rustic experience while being close to the area's natural beauty. Some properties feature amenities like hot tubs, outdoor decks, and proximity to local shops and restaurants, adding to the enjoyment of the winter getaway. These accommodations often have picturesque views of the surrounding landscape, making them an ideal choice for those looking to relax after a day on the slopes.Additionally, the nearby Chequamegon National Forest offers excellent opportunities for snowshoeing and cross-country skiing, making Ashland a great base for winter sports enthusiasts.
What is the most popular type of holiday rental accomodation in Ashland?
In Ashland, holiday houses are the most popular type of holiday rental, with about 36 available in the area. These spacious homes are often found in serene locations, providing ample room for families or groups. Most holiday houses come equipped with fully stocked kitchens, multiple bedrooms, and private outdoor spaces, allowing guests to relax and enjoy the natural surroundings. Additionally, there are around 16 apartments and approximately 12 cabins available, offering a variety of options for different preferences. The cabins, in particular, provide a rustic charm, often featuring wood interiors and access to nearby nature trails.
Are there any family house rentals in Ashland?
In Ashland, Wisconsin, there are numerous family-friendly home rentals available, with around twelve options to choose from. This charming town, located on the shores of Lake Superior, offers a range of accommodations suitable for families. Many properties provide spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces superb for kids to run around and play.Visitors can enjoy amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable and convenient stay. The local area is rich in outdoor activities, with close proximity to Chequamegon National Forest, where families can hike and explore nature trails. Additionally, the scenic Ashland Marina and nearby Apostle Islands National Lakeshore are great for family outings, providing opportunities for boating, kayaking, and enjoying the stunning views of the lake.
Are there pet-friendly house rentals in Ashland?
In Ashland, Wisconsin, there are several pet-friendly house rentals available that cater to travellers with pets. Many of these properties are situated close to the beautiful shores of Lake Superior, offering stunning views and easy access to the waterfront. Expect amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces that may include patios or decks, superb for enjoying the fresh air.The area near the Chequamegon National Forest is particularly appealing for those who enjoy outdoor activities with their pets, as it offers numerous trails for hiking and exploring. Additionally, Ashland's proximity to the Apostle Islands National Lakeshore provides opportunities for kayaking and sightseeing, making it a fantastic destination for nature enthusiasts.
Are there any remote work holiday rentals in Ashland?
In Ashland, Wisconsin, there are numerous remote work-friendly holiday rentals available, with around 52 options to choose from. The scenic surroundings of Ashland, located on the shores of Lake Superior, provide an inspiring backdrop for working remotely. Many of these rentals come equipped with essential amenities such as high-speed Wi-Fi, dedicated desks, and comfortable workspaces, ensuring that guests can maintain productivity during their stay.The area boasts charming neighbourhoods close to local attractions, including the Ashland Historical Museum and the Chequamegon Bay, superb for taking breaks and enjoying the natural beauty of the region. Additionally, some properties may feature outdoor patios or balconies, offering a pleasant environment for working or unwinding after hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Ashland?
In Ashland, popular rental amenities include well-equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature outdoor decks or patios, superb for enjoying the scenic views and fresh air. For those who enjoy their morning brew, rentals often come with coffee and tea makers, along with blenders for quick breakfasts or smoothies. Additionally, on-site parking is commonly available, making it convenient for visitors with their own vehicles.
When is the best time to visit Ashland for a holiday rental?
The peak travel season in Ashland occurs from June to August, with July being the most popular month for visitors. During this time, the area buzzes with activity as tourists flock to enjoy the beautiful summer weather, ideal for outdoor adventures and exploring the stunning Apostle Islands. The warm temperatures, typically ranging from 15 to 30 degrees Celsius, create the great environment for kayaking, hiking, and soaking up the scenic views along the shoreline.If you prefer a more tranquil experience, consider visiting in November. This month offers a unique opportunity to witness the transition of the landscape as it prepares for winter, providing a quieter atmosphere to explore Ashland's charming downtown and local art scene. The crisp air and fewer crowds can enhance your experience, allowing for leisurely strolls and reflective moments by the lake.Whether you're drawn to the vibrant summer atmosphere or the peacefulness of late autumn, Ashland has something special to offer year-round.
What are the top attractions in Ashland?
In Ashland, visitors can enjoy a range of attractions that showcase the area's natural beauty and cultural heritage. The stunning Chequamegon Bay offers opportunities for outdoor activities such as kayaking and fishing, with scenic views that are great for nature lovers. Nearby, the Apostle Islands National Lakeshore is a must-visit, known for its picturesque sea caves and hiking trails, making it ideal for those who enjoy exploring the great outdoors.The Ashland Historical Museum provides insights into the local history and heritage, featuring exhibits that highlight the region's past. For a more relaxed experience, the local parks, such as Maslowski Beach Park, offer sandy shores and picnic areas, great for a day out with family or friends.Additionally, the vibrant downtown area features unique shops, local eateries, and community events, providing visitors with a taste of the local culture.
Are all fees included in the Ashland holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Ashland holiday homes with parking?
Stayz offers a wide selection of holiday homes in Ashland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Ashland holiday homes?
You can find great discounts on holiday homes in Ashland on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Ashland holiday home booking on Stayz?
To find Ashland holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Ashland?
A long-stay holiday home in Ashland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Ashland holiday home?
Book your Ashland holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Ashland?
Prices for holiday homes in Ashland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Ashland to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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